


Family Secrets

by Stareena



Category: Supernatural
Genre: Dean Winchester is a bad man, F/M, M/M, Short Story, Sibling Incest, unknown incest
Language: English
Status: Completed
Published: 2019-12-29
Updated: 2019-12-29
Packaged: 2021-02-27 06:34:57
Rating: Mature
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,828
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22022674
Author URL: https://archiveofourown.org/users/Stareena/pseuds/Stareena
Summary: On a trip home from college, Anna swoons over friend of the family, Dean Winchester. Then everything goes wrong.
Relationships: Anna Milton/Dean Winchester
Kudos: 5





	Family Secrets

The Novaks were wealthy. The kind of wealthy where the children stayed at home with their spouses. They were the kind of wealthy where the family wasn’t all by blood. Members would pick up strays that would get absorbed into the family for a time. Which was why it was never a surprise to see a new face around the house. They could be a friend of a sister, brother, aunt, father.... You just never knew. So when Anna came home from college and brought with her several of her girlfriends with her, this was nothing new or different. The funny fact was, the house, or mansion really, was never in a state of chaos. There was always a smoothness to it. Yes, generally there were people in each room but it was never crazy.  
Anna’s arrival was exciting for the house but it came in waves as family and friends came and went. With the girls having comendered the second living room, people came and went as they pleased. With the three girls deciding to make it a proper sleepover, with sleeping bags, snacks and bad movies, it attracted her older brothers and their friends.It was somewhat upsetting to Anna, in that her brothers were flirting with her friends and they were flirting right back. The point of the sleepover was to have fun, and enjoy some time outside of school together. That was until her second oldest brother Lucifer showed up and not alone.   
As tall as her brother, his eyes were the deepest green she’d ever seen. He’d been introduced as Dean and he’d been staying with the Novaks, along with his brother Sam, for a couple of months. Something she’d remember in an email or text from another brother, Gabriel.   
“Shame isn’t it?” Gabriel asked, staring at the two newest editions to Casa de Novak.  
“What?” Anna asked, looking away from painting his toenails black, as the others in the room chatted or ate.   
“Them? The hotties, it’s such a shame about them.” Gabriel sighed and studied his toes.  
“Shame? What shame?” Anna leaned in closer, lowering her voice.  
“Don’t be stupid, Anna, you know why I can’t tap that tall moose man.”  
“Because… he’s not gay or bi?” Anna sat confused for a moment.  
“Or into… you know… me.” Gabriel raised his eyebrows.  
“Beastiality?” Anna teased.  
“Bitch.”  
“Takes one to know one.” Anna continued to paint his nails and excused the conversation from her mind despite the heated looks she was catching from Dean. As people started winding down for the night, and heading off to sleep, Anna found herself in a great conversation with Dean, talking about some of the better books into movies and books that should be movies. Catching her breath and tucking her hair back, Anna glanced around the room and realized that her two friends were passed out in their bags on the air mattresses and everyone else had gone to bed.   
“Wow, I didn’t realize it was so late.” Anna looked around and blinked.   
“Night doesn’t have to end.” Dean grinned. Looking back, she watched as the man slipped off the couch and crawled his way over to her, slithering up her body and kissing her deeply, allowing Anna to feel his excitement against her thigh.   
“Dean-” Anna whispered, pushing against his chest.  
“Be quiet,” He whispered back, glancing at the two friends, “we don’t want to wake them up now do we?”  
“No but Dean-”  
“Shhhh….” Dean held a finger up to Anna’s lips, as his other hand pulled at her boxer short pajama bottoms, working them down to her knees until he could catch them with his foot and push them down from there. Quickly Dean worked the waistband of his sweats down, kissing Anna even as she began wiggling at her partial nudity.  
“You’re so beautiful.” He whispered to her in her ear as he started to finger her. Moving her face from his, she moved her hands to push at his chest again.  
“Dean, please…”  
Stopping, he pushed up, “You don’t want me? I thought you were interested.” Taking his middle finger out of her, he sucked on it deeply, “Seems to me like you’re kinda into this. But if you really want me to stop, I will.” Anna’s eyes went large and round staring at him. Dean used the hesitation, to roll his hips against hers, stimulating her clit, causing her to roll her eyes back. “Do you want me to stop or do you want me to make you cum harder than you’ve ever cum in your life?”  
Suddenly she was panting.  
“It’s hot isn’t it? Doing it, like this... you and I?” He kissed up her neck towards her ear, “But you have to be quiet, so very quiet. Even when you cum. We don’t want to wake anyone else do we?”  
Anna shook her head no, words were beyond her. Did she want this? It seemed like a bad idea to her a few minutes ago but for the life of her she couldn’t remember why.  
“Can you be a good girl, Anna?”  
“Yes.” She whispered back.  
“Cause if you’re bad, I’ll have to punish you. And I won’t be soft in my punishments.” Dean grinned before lining himself up and pushing in fully. Anna cried out before Dean covered her mouth with his hand, “I see punishment is to be had.” He snickered darkly, “This should be fun.” Pulling back he snapped his hips forward with significant force, causing Anna to cry out against his hand again, her eyes wincing from the pain. Her body not yet accustomed to his size yet. Repeating his actions, Dean set a punishing pace, fucking into Anna brutally. After a short amount of time, Dean growled and switched up slightly, keeping Anna’s mouth covered, but using his other hand to close around her throat as he fucked into her. Easing back on his thrusts, he kept his orgasam at bay by rolling his hips more than snapping them. When Anna’s noises quieted, he removed his hands from her upper body, and began kissing her deeply. Mewling and whining into the kisses, Dean ensured that as he rolled his hips, he was going in deeply, while he moved his hand between their bodies. Finding her stiffened bud, he rolled it around with his middle finger, swirling it around, causing her body to buck and arch, still, he kept his thrusts slower and languid, even with Anna’s body tightening around him life a vice.   
It was when she arched her back entirely, her warmth a clamp around his cock and her lungs drawing ragged breath that he grabbed her by the throat again with his left hand, even as he continued rubbing her with his right. This time though, he fucked into her hard all over again, his rhythm off and erratic.   
“DDDDean…..” Her body bucked, and before she realized it, she felt a warmth within her, “Nononononono…”  
“Gah!” Dean sighed as he finished orgasaming himself. Releasing her throat and allowing her to catch her breath, causing her whole body to shiver and shake with another orgasm. “Fuck.” Dean whispered as he steadied himself, “Sister, you are something else.”  
Panting, Anna laid back and tried to process everything that just happened. Rubbing her neck she wondered if she would have bruises later, she didn’t want to have to explain those to anyone.  
“I cannot wait to tap that ass again, later.” Dean smirked, rolling over and grabbing a cigarette from the coffee table.  
“What makes you think there will be another time?” Anna asked.  
“Because there will be.” Dean replied lighting up, “Or do you want to explain to our parents about us fucking?”  
“Why would I have to do that?”  
“Uh, I’m sure they would want to know why their kids are fucking each other.” Dean frowned and took a drag off the smoke.   
Anna stared at him for a long moment. There was something that she was missing here.  
“Why would your parents or my parents care about us fucking?” Anna asked carefully.  
“Um, because our Daddy is the same person.” Dean flicked the ashes in the ashtray, “And since I saw your pics for the first time, I knew I had to get a taste of your sweet puss, I’m so glad that I did.”  
Sitting in shock Anna sat looking at Dean.  
“Don’t look at me like that, Gabriel was the one that told you we were related, I heard him talking with you earlier. And besides, I know Lucifer has a thing for Sammy. I told him he can have Sammy if I can have you, we agreed to it.” He took another drag.  
“Have?”  
“Oh yeah babe, you have no idea the plans we have in store for you.” Dean smiled.  
“This is ridiculous, I’m going to talk with my father.” Anna stood up and started for the doorway.  
“And tell him what exactly? That you just had sex with your half brother? That it was not exactly consensual?” Dean set his cigarette down in the ashtray and walked over to her frozen form in the doorway, “How is your relationship with your father Anna? When was the last time you walked with him? Hmm? How did that go? Did he approve of your boyfriends? Your girlfriends? Your drinking? What about the time you pierce your nipple?” Dean twisted her left nipple a little too hard, “Daddy’s been in my life since I was sixteen. From the moment he found out about Sammy and I, he was right there, and boy let me tell you, he loves me. I can do no wrong in his eyes, so let me ask you, how do you think that conversation will go Anna?” Dean whispered into her ear, “Bad things happen when you talk.”  
He stepped back and layed back down on the mattress and took up his cigarette again and finished off watching her.   
Turning around, Anna had tears in her eyes, “Please,”.  
“Do as I say and it will make everything easier.” Dean said, holding his hand out to her.  
She hesitated a moment before crawling back onto the bed.  
“Good girl.” He whispered, “But I want to take you someplace where you can be loud, so it’s off to my room.”  
Anna looked up in panic.  
“Like I said, I have plans for you and one of them is to mark you as mine.” Dean stood, fully nude and unashamed. Pulling Anna to her feet, he dragged her towards his room across the mansion.  
“How do you intend to mark me?” Anna asked weakly, hoping a simple hickey would suffice. Stopping outside of a door, Dean turned and regarded his half-sister a moment before grinning.  
“I think knocking you up will work.” He nodded.  
“Wha-”   
Anna was yanked into Dean’s room followed by a slam of his door. An exclamation point to his declaration on the matter.


End file.
